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Upstream product

• 190438-31-4 tert-butyl (2S,3R,4S)-3-hydroxy-2-hydroxymethyl-4-[(11S)-11-hydroxy-13-methyltetradecyl]azetidine-1-carboxylate 
• 603127-04-4 (2S,3R,4S)-3-Methoxymethoxy-2-methoxymethoxymethyl-4-((S)-11-methoxymethoxy-13-methyl-tetradecyl)-azetidine-1-carboxylic acid tert-butyl ester 
• 691-37-2 4-Methyl-1-pentene 
• 23850-78-4 4-methyl-1,2-epoxypentane 
• 60856-89-5 2-(R)-isobutyl-oxirane 
• 629-05-0 n-octyne 

Relevant academic research and scientific papers

Divergent total synthesis of penaresidin B and its straight side chain analogue

The divergent synthesis of penaresidin B and its straight side chain analogue was accomplished by constructing an azetidine ring via SN2 type cyclization of protected 2,3-syn-3,4-syn-4-amino-1,3-dihydroxyhept-6-en-2-yl mesylate and late-stage introduction of an alkyl side chain via olefin cross-metathesis of 4-allylazetidine with readily available terminal alkenes. This synthetic route would be useful to synthesize penaresidin side chain analogues.

Intermolecular sp3-C-H Amination for the Synthesis of Saturated Azacycles

The preparation of substituted azetidines and larger ring, nitrogen-containing saturated heterocycles is enabled through efficient and selective intermolecular sp3-C-H amination of alkyl bromide derivatives. A range of substrates are demonstrated to undergo C-H amination and subsequent sulfamate alkylation in good to excellent yield. N-Phenoxysulfonyl-protected products can be unmasked under neutral or mild basic conditions to yield the corresponding cyclic secondary amines. The preparative convenience of this protocol is demonstrated through gram-scale and telescoped multistep procedures. Application of this technology is highlighted in a nine-step total synthesis of an unusual azetidine-containing natural product, penaresidin B.

Novel and practical asymmetric synthesis of an azetidine alkaloid, penaresidin B

A novel and efficient asymmetric synthesis of the potent actomyosin ATPase activator, penaresidin B, is described in a short and complete stereoselective manner by featuring the elaboration of the fully functionalized homochiral lactam, which can also be

Synthesis of sphingosine relatives. Part 19. Synthesis of penaresidin A and B, azetidine alkaloids with actomyosin ATPase-activating properties

Three stereoisomers of penaresidin A 1 and two stereoisomers of penaresidin B 2' (Scheme 5), azetidine alkaloids isolated from the Okinawan marine sponge Penares sp., have been synthesized.In the course of our synthetic study, the correct structure of penarisidin B has been shown to be not 2 but 2'.Natural penaresidin A is either (2S,3R,4S,15S,16S)- or (2S,3R,4S,15R,16R)-1 and natural penaresidin B is either (2S,3R,4S,15S)- or (2S,3R,4S,15R)-2'.

Novel asymmetric synthesis of penaresidin B as a potent actomyosin ATPase activator

An efficient and novel synthetic process is described for the preparation of an azetidine ring with the contiguous stereogenic centers and the total synthesis of penaresidin B by featuring the elaboration ofthe functionalized homochiral lactam derived from D-glutamic acid.